4548-45-2

Basic information

• Product Name: 2-Chloro-5-nitropyridine
• Synonyms: 2-Chloro-5-nitropyridine;3-Nitro-6-chloropyridine;5-Nitro-2-chloropyridine;6-Chloro-3-nitropyridine;2-Chloro-5-nitropyridine, 99% 25GR;2-Chloro-5-nitropyridine, 97+%;Chloro-5-nitropyrid;4548-45-2
• CAS NO: 4548-45-2
• Molecular Formula: C₅H₃ClN₂O₂
• Molecular Weight: 158.54252
• EINECS: 224-908-3
• Product Categories: Pyridine series;Halides;Pyridines derivates;Chloropyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Chlorinated heterocyclic series;alkyl chloride |nitro-compound;compounds of pyridine;blocks;Pyridines;Pyridine;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 4548-45-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 106 °C
• Boiling Point: 256.6 °C at 760 mmHg
• Flash Point: 158°C
• Appearance: Light yellow to beige/Crystalline Powder
• Density: 1.6616 (rough estimate)
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -4.22±0.10(Predicted)
• Water Solubility: Solubility in hot methanol. Insoluble in water.
• BRN: 120453
• CAS DataBase Reference: 2-Chloro-5-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-5-nitropyridine(4548-45-2)
• EPA Substance Registry System: 2-Chloro-5-nitropyridine(4548-45-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: US7175000
• HazardClass: IRRITANT
• Hazardous Substances Data: 4548-45-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal

Uses

2-Chloro-5-nitropyridine is used as a pharmaceutical intermediate.

Purification Methods

It crystallises from *benzene or *benzene/pet ether. [Beilstein 20/5 V 452.]

InChI:InChI=1/C5H3ClN2O2/c6-5-4(8(9)10)2-1-3-7-5/h1-3H

Upstream product

• 5418-51-9 5-nitro-2-hydroxypyridine 
• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 2403-01-2 3-nitropyridine N-oxide 
• 2530-26-9 3-nitropyridine 
• 504-29-0 2-aminopyridine 
• 444120-91-6 6-chloropyridin-3-ylboronic acid 
• 4487-59-6 2-bromo-5-nitropyridine 
• 64-17-5 ethanol 
• 147-85-3 L-proline 
• 2554-75-8 N,N-dimethyl-5-nitropyridin-2-amine 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 7647-01-0 hydrogenchloride 
• 31594-45-3 2-ethoxy-5-nitropyridine 

Downstream Products

• 99387-23-2 5-nitro-2-propoxypyridine 
• 76893-52-2 2-(3,4-Dimethyl-phenoxy)-5-nitro-pyridine 
• 76893-46-4 2-(4-ethylphenoxy)-5-nitropyridine 
• 76893-56-6 2-(4-isopropylphenoxy)-5-nitropyridine 
• 76893-49-7 2-[(2,6-dimethylphenyl)oxy]-5-nitropyridine 
• 20885-21-6 3-nitro-6-(methylthio)pyridine 
• 116470-66-7 5-nitro-2-(trifluoromethyl)pyridine 
• 914223-27-1 tert-butyl 2-cyano-2-(5-nitropyridin-2-yl)acetate 
• 76893-54-4 2-[(2,3-dimethylphenyl)oxy]-5-nitropyridine 
• 25935-29-9 2-(3,4-dichlorophenoxy)-5-nitropyridine 
• 88912-74-7 2-chloro-5-nitro-4-(phenylsulfonylmethyl)pyridine 
• 111986-64-2 3-Methyl-4-(5-nitro-pyridin-2-yloxy)-phenylamine 
• 21203-68-9 2-methyl-5-nitropyridine 
• 28222-02-8 3-nitro-6-phenoxypyridine 

Relevant articles and documents

Deaminative chlorination of aminoheterocycles

Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]

Methnaridine is an orally bioavailable, fast-killing and long-acting antimalarial agent that cures Plasmodium infections in mice

Background and Purpose: Malaria is one of the deadliest diseases in the world. Novel chemotherapeutic agents are urgently required to combat the widespread Plasmodium resistance to frontline drugs. Here, we report the discovery of a novel benzonaphthyridine antimalarial, methnaridine, which was identified using a structural optimization strategy. Experimental Approach: An integrated pharmacological approach was used to evaluate the antimalarial profile of methnaridine. The pharmacokinetic properties of methnaridine were investigated along with the associated safety profile. Host immune response patterns were also analysed. Key Results: Methnaridine exhibited potent antimalarial activity against P. falciparum (3D7: IC50 = 0.0066 μM; Dd2: IC50 = 0.0056 μM). In P. berghei-infected mice, oral administration effectively suppressed parasitemia (ED50 = 0.52 mg·kg?1·day?1) and cured the established infection (CD50 = 10.13 mg·kg?1·day?1). These results are equivalent to or better than those of other antimalarial agents in clinical use. Notably, a four-dose oral regimen at a dosage of 25 mg·kg?1 achieved a complete cure of P. berghei infection in mice. Methnaridine exhibited a rapid parasiticidal profile (PCT99 = 36.0 h) and showed no cross-resistance to chloroquine. Pharmacokinetic studies revealed that methnaridine is readily absorbed, long-lasting and slowly cleared. The safety profile of methnaridine is also satisfactory (maximum tolerated dose = 1,125 mg·kg?1). In addition, following methnaridine treatment, infection-induced Th1 immune response was almost fully alleviated in mice. Conclusion and Implications: Methnaridine is an orally bioavailable, fast-acting and long-lasting agent with excellent antimalarial properties. Our study highlights the potential of methnaridine for clinical development as a promising antimalarial candidate.

Preparation method of 2-chloro-5-nitropyridine

The invention provides a preparation method of 2-chloro-5-nitropyridine. The preparation method comprises the following steps: preparing 2-hydroxy-5-nitropyridine by taking 2-nitroacetaldehyde diethylacetal as an initial raw material through two methods; and then carrying out a chlorination reaction on the 2-hydroxy-5-nitropyridine and a chlorination reagent to prepare the 2-chloro-5-nitropyridine. The method has the advantages of cheap and accessible raw materials and low cost, does not use a diazotization hydrolysis reaction, is safe, simple and convenient to operate, does not use mixed acid, is less in wastewater yield and environmentally-friendly, does not use a nitration reaction, is high in reaction selectivity, few in side reactions, simple in post-treatment and high in product yield and product, and is suitable for industrial production.

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Preparation method of high-yield 2-chloro-5-nitropyridine

The invention relates to a preparation method of high-yield 2-chloro-5-nitropyridine. According to the method, 2-halogenated acrylate serves as an initial raw material and is sequentially condensed with nitromethane and triethyl orthoformate and cyclized with pyridine to obtain 2-hydroxy-5-nitropyridine, and then the 2-chloro-5-nitropyridine is prepared by chlorination. Used raw materials are lowin cost and easy to obtain, operation is simple and convenient, conditions are mild, nitration reaction is omitted, wastewater quantity is small, operation safety is high, product yield and purity arehigh, and the cost is low.

Preparation method for preparing 2-chloro-5-nitropyridine from dichlorine monoxide

The invention aims at providing a preparation method for preparing 2-chloro-5-nitropyridine from dichlorine monoxide. The problems can be solved for realizing easy production, high yield, low cost andlow pollution of 2-chloro-5-nitropyridine. The preparation method comprises the following steps of uniformly mixing 3-nitropyridine, alkali, chlorate and solvents; performing low-temperature coolingto -15 to -10 DEG C; under the sufficient stirring, dissolving dichlorine monoxide into the solvents; dripping the materials into a reaction mixed solution; maintaining the temperature at -10 DEG C to0 DEG C; completing the dripping in 2 hours; raising the temperature to the room temperature; continuously stirring the materials for 2 hours until 3- nitropyridine completely reacts; pouring reactants into ice water; separating an organic layer; collecting the organic layer; washing the organic layer by hydrochloric acid with the mass concentration being 5 percent; performing water washing once;performing drying by anhydrous magnesium sulfate; performing reduced pressure distillation to remove organic solvents to obtain 2-chloro-5-nitropyridine. The preparation method has the advantages that the raw materials are rich; the preparation method is simple; the cost is low; the production and the preparation are easy; the yield is high; the energy is saved; the environment is protected; theeconomic and social benefits are huge.

Preparation method for malaridine intermediate 2-methoxy-5-aminopyridine

The invention provides a green environment-friendly preparation method for a malaridine intermediate 2-methoxy-5-aminopyridine. The preparation method comprises the specific method: with 2-aminopyridine as a raw material, nitrating 2-aminopyridine with a mixed acid in the presence of a solvent to obtain 2-amino-5-nitropyridine; and carrying out hydrolysis, chlorination, methoxylation and reduction to obtain the intermediate 2-methoxy-5-aminopyridine. The preparation method has the advantages of simple process, short production cycle, mild reaction conditions, fewer three wastes, high product purity and yield, cheap and easily obtained raw materials, and higher economic property and environmental protection, and is suitable for industrialized production.

One-Pot C?H Functionalization of Arenes by Diaryliodonium Salts

A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryliodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.

A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids

A mild, convenient and transition metal free methodology for oxidative ipso nitration of diversely functionalized organoboronic acids, including heteroaryl- and alkylboronic acids, has been developed at ambient temperature using a combination of [bis-(trifluoroacetoxy)]iodobenzene (PIFA) - N-bromosuccinimide (NBS) and sodium nitrite as the nitro source. It is anticipated that the reaction proceeds through in situ generation of NO2 and O-centred organoboronic acid radicals followed by the formation of an O-N bond via combination of the said radicals. Finally transfer of the NO2 group to the aryl moiety occurs through 1,3-aryl migration to provide the nitroarenes.

SUBSTITUTED HETEROAROMATIC PYRAZOLE-CONTAINING CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted heteroaromatic pyrazole-containing carboxamide and urea derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.